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Direct Oxidative Amidation between N,N-dimethylanilines and Anhydrides Using Metal-Organic Framework [Cu2(EDB)2(BPY)] as an Efficient Heterogeneous Catalyst

Authors

  • Giao H. Dang,

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504
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  • Thanh D. Nguyen,

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504
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  • Dung T. Le,

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504
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  • Thanh Truong,

    Corresponding author
    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504
    • Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504===

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  • Nam T. S. Phan

    Corresponding author
    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504
    • Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Viet Nam), Fax: (+84) 8-38637504===

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  • EDB=4,4′-ethynyldibenzoic acid, BPY=4,4′-bipyridine

Abstract

A crystalline porous metal-organic framework [Cu2(EDB)2(BPY)] was synthesized and used as a heterogeneous catalyst for the direct oxidative amidation between N,N-dimethylanilines and anhydrides to form tertiary amides as the principal products. The [Cu2(EDB)2(BPY)] exhibited similar activity as compared to that of [Cu2(BDC)2(BPY)], [Cu2(BDC)2(DABCO)], MOF-143, and other common homogeneous salt catalysts. The optimal reaction conditions employed were [Cu2(EDB)2(BPY)] (10 % mol), TBHP (2 equiv), pyridine (1 equiv) in CH3CN at 80 °C over 2 h. The Cu2(EDB)2(BPY) could be separated from the reaction mixture by filtration, and could be recovered and reused several times without a significant degradation in catalytic activity and selectivity. Furthermore, generality of the optimal conditions was confirmed by employing various N,N-dimethylaniline and anhydride derivatives.

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